Answer
The following synthetic conversion can be obtained through addition of $H_2SO_4$ with heat and then Halohydrins mechanism.
Work Step by Step
The reaction of $H_2SO_4$ in presence of heat gives a double bond by deprotonating OH. Then on this double bond the halohydrin mechanism is performed.
The mechanism that gives this product is the addition of Halohydrins:
1) Electrophilic attack forms a chloronium ion.
2) Back-side attack by water on the most substituted carbon opens the chloronium ion.
3) Water removes a proton to give the chlorohydrin.
Product + enantiomer formed.